Water soluble homogeneous catalysts that are recoverable by phase selectivity and host-guest interactions

Patent metadata

Field	Value
Publication number	US-10737255-B2
Application number	US-201916373817-A
Country	US
Kind code	B2
Filing date	Apr 3, 2019
Priority date	Aug 22, 2016
Publication date	Aug 11, 2020
Grant date	Aug 11, 2020

Abstract

A chemical reaction is catalyzed in an organic solvent using a water soluble N-heterocyclic carbene homogeneous catalyst to form a reaction mixture. An aqueous phase in the reaction mixture. A solvent in which the catalyst is insoluble is added to the reaction mixture, causing the catalyst to migrate to the aqueous phase to form a catalyst-laden aqueous phase. The catalyst is extracted from the catalyst-laden aqueous phase.

First claim

That which is claimed is:

1. A method comprising:
catalyzing a chemical reaction in an organic solvent using a water soluble N-heterocyclic carbene homogeneous catalyst to form a reaction mixture;
forming an aqueous phase in the reaction mixture;
adding a solvent in which the catalyst is insoluble to the reaction mixture causing the catalyst to migrate to the aqueous phase to form a catalyst-laden aqueous phase; and
extracting the catalyst-laden aqueous phase from the reaction mixture;
wherein the catalyst includes a transition metal bonded to an N-heterocyclic carbene moiety bonded to a polyethylene glycol functional group bonded to a terminal adamantyl group.

2. The method of claim 1 , wherein the solvent in which the catalyst is insoluble is an ether.

3. The method of claim 1 , wherein the solvent in which the catalyst is insoluble is diethyl ether.

4. The method of claim 1 , wherein the chemical reaction is an olefin metathesis reaction.

5. The method of claim 1 , wherein the catalyst includes the formula

and n is the number of ethylene glycol monomers in the formula.

6. A composition comprising a water soluble homogeneous catalyst including a transition metal complex having an N-heterocyclic carbene ligand with a polyethylene glycol group thereon, further comprising a terminal adamantyl group bonded to the polyethylene glycol group.

7. The composition of claim 6 , wherein the catalyst includes the formula

and n is the number of repeats of ethylene glycol in the formula.

8. The composition of claim 6 , further comprising a cyclodextrin bound to the catalyst, the catalyst and cyclodextrin forming a host-guest compound.

9. A composition comprising a water soluble homogeneous catalyst including a transition metal complex having an N-heterocyclic carbene ligand with a polyethylene glycol group thereon, further comprising a cyclodextrin bound to the catalyst, the catalyst and cyclodextrin forming a host-guest compound.

10. The composition of claim 9 , further comprising a terminal adamantyl group bonded to the polyethylene glycol group.

11. The composition of claim 9 , wherein the catalyst includes the formula

and n is the number of repeats of ethylene glycol in the formula.

12. A method comprising:
catalyzing a chemical reaction in an organic solvent using a water soluble N-heterocyclic carbene homogeneous catalyst to form a reaction mixture;
forming an aqueous phase in the reaction mixture;
adding a solvent in which the catalyst is insoluble to the reaction mixture causing the catalyst to migrate to the aqueous phase to form a catalyst-laden aqueous phase; and
extracting the catalyst-laden aqueous phase from the reaction mixture using a cyclodextrin bound to the catalyst, the catalyst and cyclodextrin forming a host-guest compound.

13. The method of claim 12 , wherein the catalyst includes a polyethylene glycol functional group.

14. The method of claim 12 , wherein the catalyst includes a transition metal bonded to an N-heterocyclic carbene moiety bonded to a polyethylene glycol functional group.

15. The method of claim 12 , wherein the catalyst includes a transition metal bonded to an N-heterocyclic carbene moiety bonded to a polyethylene glycol functional group bonded to a terminal adamantyl group.

16. The method of claim 12 , wherein the catalyst includes the formula

and n is the number of ethylene glycol monomers in the formula.

Assignees

• Univ Florida State Res Found

Inventors

• Chung Hoyong

Classifications

• B01J2540/64

  Solubility enhancing groups · CPC title

• B01J2540/10

  Non-coordinating groups comprising only oxygen beside carbon or hydrogen · CPC title

• B01J31/4038

  containing noble metals · CPC title

• C07D209/48

  with oxygen atoms in positions 1 and 3, e.g. phthalimide · CPC title

• C08B37/0015

  Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes · CPC title